21744-83-2

Usage

Uses

Used in Agricultural Industry:
2-Methyl-[1,4] Benzoxazin-3(4H)-one is used as a natural herbicide for its allelopathic properties, which help inhibit the growth of competing plants. This allows for more efficient crop growth and reduced competition for resources, ultimately leading to higher crop yields.
Used in Pharmaceutical Industry:
2-Methyl-[1,4] Benzoxazin-3(4H)-one is used as an antimicrobial agent due to its ability to inhibit the growth of certain microorganisms. This makes it a potential candidate for the development of new antibiotics or other antimicrobial treatments.
Additionally, 2-Methyl-[1,4] Benzoxazin-3(4H)-one is used as an antioxidant in the pharmaceutical industry. Its antioxidant properties can help protect cells from damage caused by reactive oxygen species, which may contribute to various diseases and aging processes. This makes it a promising compound for the development of treatments targeting oxidative stress-related conditions.

InChI:InChI=1/C9H9NO2/c1-6-9(11)10-7-4-2-3-5-8(7)12-6/h2-6H,1H3,(H,10,11)

Upstream product

• 21744-73-0 2-methyl-4H-benzo[1,4]oxazine-3-thione 
• 7623-09-8 2-chloropropionyl chloride 
• 95-55-6 2-amino-phenol 
• 535-11-5 Ethyl 2-bromopropionate 
• 42412-84-0 ethyl 2-phenoxypropionate 
• 1248721-80-3 2-(2-nitrophenoxy)propanenitrile 
• 88-75-5 2-hydroxynitrobenzene 
• 5445-17-0 Methyl 2-bromopropionate 
• 34373-88-1 2-(2-Chlorophenoxy)propionamide 
• 90923-22-1 α-(2-Nitrophenoxy)-propionsaeure-methylester 
• 139-02-6 sodium phenoxide 
• 940-31-8 2-phenoxypropionic acid 
• 90561-87-8 2-(2-bromo-propionylamino)-phenol 
• 13212-57-2 2-(2-nitrophenoxy)propanoic acid 

Downstream Products

• 17959-80-7 2-[2-(3,4-Dichloro-benzoylamino)-phenoxy]-propionic acid 
• 221311-16-6 6-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 352666-89-8 C₁₂H₁₃NO₄ 

Relevant academic research and scientific papers

Efficient synthesis of benzene-fused 6/7-membered amides: Via Xphos Pd G2 catalyzed intramolecular C-N bond formation

An efficient approach for benzene-fused 6/7-membered amides via intramolecular amidation of aryl chlorides catalyzed by a Buchwald-Hartwig second generation Pd catalyst (Xphos Pd G2) has been successfully developed. This catalyst system allows the primary amides which have only modest nucleophilicity to be coupled successfully even with electron rich aryl chlorides in short reaction time. The intramolecular amidation reaction also has good chemoselectivity and excellent functional group compatibility.

Benzomorpholone derivative as well as preparation method and application of benzomorpholone derivative

The invention belongs to the field of chemical medicines and particularly relates to a benzomorpholone derivative as well as a preparation method and application of the benzomorpholone derivative. The invention provides a benzomorpholone derivative with a structure as shown in the formula I and also provides a preparation method and application of the benzomorpholone derivative. The benzomorpholone derivative provided by the invention is novel in structure, has a good effect on selectively inhibiting BET targets, produces cytotoxicity for various tumor cells to different extents and is a novel BET small-molecule inhibitor. The compound disclosed by the invention has the potential to develop antitumor drugs.

Development of small-molecule Trypanosoma brucei N-myristoyltransferase inhibitors: Discovery and optimisation of a novel binding mode

The enzyme N-myristoyltransferase (NMT) from Trypanosoma brucei has been validated both chemically and biologically as a potential drug target for human African trypanosomiasis. We previously reported the development of some very potent compounds based around a pyrazole sulfonamide series, derived from a high-throughput screen. Herein we describe work around thiazolidinone and benzomorpholine scaffolds that were also identified in the screen. An X-ray crystal structure of the thiazolidinone hit in Leishmania major NMT showed the compound bound in the previously reported active site, utilising a novel binding mode. This provides potential for further optimisation. The benzomorpholinone was also found to bind in a similar region. Using an X-ray crystallography/structure-based design approach, the benzomorpholinone series was further optimised, increasing activity against T. brucei NMT by >1000-fold. A series of trypanocidal compounds were identified with suitable in vitro DMPK properties, including CNS exposure for further development. Further work is required to increase selectivity over the human NMT isoform and activity against T. brucei. HATs off to diversity! Screening a diverse library against Trypanosoma brucei N-myristoyltransferase (NMT) identified hits based on thiazolidinone and benzomorpholine scaffolds. X-ray crystallography of these compounds bound to Leishmania major NMT revealed novel active site binding conformations. Using the structural information, the benzomorpholine scaffold was optimised to a blood-brain barrier penetrant compound with activity against TbNMT of 0.002 μm.

A series of potent crebbp bromodomain ligands reveals an induced-fit pocket stabilized by a cation-π interaction

The benzoxazinone and dihydroquinoxalinone fragments were employed as novel acetyl lysine mimics in the development of CREBBP bromodomain ligands. While the benzoxazinone series showed low affinity for the CREBBP bromodomain, expansion of the dihydroquino

Discovery of novel benzo[b][1,4]oxazin-3(4H)-ones as poly(ADP-ribose) polymerase inhibitors

Structure based drug design of a series of novel 1,4-benzoxazin-3-one derived PARP-1 inhibitors are described. The synthesis, enzymatic & cellular activities and pharmacodynamic effects are described. Optimized analogs demonstrated inhibition of poly-ADP-ribosylation in SW620 tumor bearing nude mice through 24 h following a single dose.

A simple and facile route for the synthesis of 2H-1,4-benzoxazin-3-(4H)- ones via reductive cyclization of 2-(2-nitrophenoxy)acetonitrile adducts in the presence of Fe/acetic acid

A simple route for the synthesis of 1,4-benzoxazin-3-(4H)-ones is described herein. This method involves the reductive cyclization of 2-(2-nitrophenoxy) acetonitrile adducts in the presence of Fe/acetic acid in good to excellent yields. This system was compatible with various other functional groups.

Inductive heating with magnetic materials inside flow reactors

Superparamagnetic nanoparticles coated with silica gel or alternatively steel beads are new fixed-bed materials for flow reactors that efficiently heat reaction mixtures in an inductive field under flow conditions. The scope and limitations of these novel heating materials are investigated in comparison with conventional and microwave heating. The results suggest that inductive heating can be compared to microwave heating with respect to rate acceleration. It is also demonstrated that a very large diversity of different reactions can be performed under flow conditions by using inductively heated flow reactors. These include transfer hydrogenations, heterocyclic condensations, pericyclic reactions, organometallic reactions, multicomponent reactions, reductive cyclizations, homogeneous and heterogeneous transition-metal catalysis. Silica-coated iron oxide nanoparticles are stable under many chemical conditions and the silica shell could be utilized for further functionalization with Pd nanoparticles, rendering catalytically active heatable iron oxide particles.

[Omim][BF4], a green and recyclable ionic liquid medium for the one-pot chemoselective synthesis of benzoxazinones

An efficient procedure for the one-pot chemoselective synthesis of 2H-benzo[b][1,4]oxazin-3(4H)-one derivatives from their corresponding o-aminophenols is developed using DBU in the ionic liquid [omim][BF4]. Upon completion of the reaction and separation of the product, the ionic liquid is recovered and successfully reused over nine recycles without any noticeable loss of performance.

Microwave-assisted one-pot regioselective synthesis of 2-alkyl-3,4-dihydro- 3-oxo-2H-1,4-benzoxazines

A protocol for regioselective one-pot synthesis of 2-alkyl-3,4-dihydro-3- oxo-2H-1,4-benzoxazines under controlled microwave heating has been developed. Starting from commercially available 2-aminophenols, a base-mediated regioselective O-alkylation took

6-BENZOXAZINYL- AND 6-BENZOTHIAZINYL 2,3,4,5-TETRAHYDROPYRIDAZIN-3-ONES

The synthesis of benzoxazinyl- and benzothiazinylpyridazinone compounds is described. The novel compounds are cardiotonic agents and inhibitors of phosphodiesterase. In addition, the compounds are useful as smooth muscle relaxants and bronchodilators